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What happens if I try to charge 2 cars at the same time?

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None of that is true. The J1772 wall connectors are based on a Gen2. They were built long before the Gen3 was ever created. Tesla just didn't sell them to the public before now. It has no wi-fi connectivity, so it obviously can't communicate with Gen3 wall connectors. It only has the twisted pair direct wiring for sharing, and it can only share specifically with other Gen2 type units that have the 50A limit, of which two types are available: this J1772 kind or the older ones that came with a 14-50 cord attached, but those are kind of rare.

Yes, you are correct. It can't share with Gen3 ones at all.
This is correct. I was looking at having a Tesla and a J1772 power sharing (replacing a 3 with a Rivian in 202x) but right now it’s not possible. I can’t imagine why this is better from a manufacturing perspective.
One would think power-sharing will be very common in households at the front of ev adoption, and Tesla doing a first move for those use cases and the valuable data it generates seems like a no brainer. When x% of the grid energy will go to EVs, having telemetry at the instance level would be gold for things like autobidder. (note, I don’t believe they do any of this or have TOU that allow to do any of this right now)
 
I was looking at having a Tesla and a J1772 power sharing (replacing a 3 with a Rivian in 202x) but right now it’s not possible. I can’t imagine why this is better from a manufacturing perspective.
Huh? I haven't heard anyone claiming anything here is "better". It's a limitation they have because of the J1772 cables/handles they are using. They won't support 80A, so it's something they have to do for safety. So those have to be limited to 40A. And since the install style of the older version 2 wall connectors is where all have to be set for the same amps and allowed Polaris bonding the power connections together instead of separate breakers, they just have to enforce that limit of 50A circuit on all of these that will be hooked together for sharing.
 
Huh? I haven't heard anyone claiming anything here is "better". It's a limitation they have because of the J1772 cables/handles they are using. They won't support 80A, so it's something they have to do for safety. So those have to be limited to 40A. And since the install style of the older version 2 wall connectors is where all have to be set for the same amps and allowed Polaris bonding the power connections together instead of separate breakers, they just have to enforce that limit of 50A circuit on all of these that will be hooked together for sharing.
My point is, why would they not just manufacture gen3 wall connectors for both terminations; instead of maintaining two sets (gen 2 and gen 3) of casings, electronics, etc in supply, under warranty, etc. It seems better to reduce supply complexity AND use first mover advantage on setting up an easier to extend system for the 2nd EV. And of course make the J1772 gen 3 able to deliver 60A/48A just like the Tesla connector sibling.
 
My point is, why would they not just manufacture gen3 wall connectors for both terminations;
Because these were designed and built SEVERAL years ago, before the Gen3 wall connector existed. They just used it for their own purposes, installing them at some sites where they were required to provide some general purpose charging by agreements with cities or businesses. And as people noticed, they put this up for sale on their website, and they sold out quickly, and now the page is gone, so they seemed to be just liquidating their old leftover stock of these.

instead of maintaining two sets (gen 2 and gen 3) of casings, electronics, etc in supply, under warranty, etc. It seems better to reduce supply complexity AND use first mover advantage on setting up an easier to extend system for the 2nd EV.
That IS what they were doing. They made this long ago, when the Gen2 was the only one that existed. So they had main Gen2 bodies, with most parts in common, and had two types of cables for them, exactly as you are suggesting.
And of course make the J1772 gen 3 able to deliver 60A/48A just like the Tesla connector sibling.
That may be something they will consider doing now that they sold out their remaining stock of those and have discontinued the Gen2 and have replaced it with the Gen3. I would put my estimate at about 40% confidence that they will do that.